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Facile Access to 2-Selenoxo-1,2,3,4-tetrahydro-4-quinazolinone Scaffolds and Corresponding Diselenides via Cyclization between Methyl Anthranilate and Isoselenocyanates: Synthesis and Structural Features.

ABSTRACT: A practical method for the synthesis of 2-selenoxo-1,2,3,4-tetrahydro-4-quinazolinone was reported. The latter compounds were found to undergo facile oxidation with H2O2 into corresponding diselenides. Novel organoselenium derivatives were characterized by the 1H, 77Se, and 13C NMR spectroscopies, high-resolution electrospray ionization mass spectrometry, IR, elemental analyses (C, H, N), and X-ray diffraction analysis for several of them. Novel heterocycles exhibited multiple remarkable chalcogen bonding (ChB) interactions in the solid state, which were studied theoretically.

SUBMITTER: Osmanov VK 

PROVIDER: S-EPMC9504104 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Facile Access to 2-Selenoxo-1,2,3,4-tetrahydro-4-quinazolinone Scaffolds and Corresponding Diselenides via Cyclization between Methyl Anthranilate and Isoselenocyanates: Synthesis and Structural Features.

Osmanov Vladimir K VK   Chipinsky Evgeniy V EV   Khrustalev Victor N VN   Novikov Alexander S AS   Askerov Rizvan Kamiloglu RK   Chizhov Alexander O AO   Borisova Galina N GN   Borisov Alexander V AV   Grishina Maria M MM   Kurasova Margarita N MN   Kirichuk Anatoly A AA   Peregudov Alexander S AS   Kritchenkov Andreii S AS   Tskhovrebov Alexander G AG  

Molecules (Basel, Switzerland) 20220907 18

A practical method for the synthesis of 2-selenoxo-1,2,3,4-tetrahydro-4-quinazolinone was reported. The latter compounds were found to undergo facile oxidation with H<sub>2</sub>O<sub>2</sub> into corresponding diselenides. Novel organoselenium derivatives were characterized by the <sup>1</sup>H, <sup>77</sup>Se, and <sup>13</sup>C NMR spectroscopies, high-resolution electrospray ionization mass spectrometry, IR, elemental analyses (C, H, N), and X-ray diffraction analysis for several of them. N  ...[more]

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